A stereospecific pathway for the introduction of deuterium or tritium on the brassinosteroid skeleton by reductive dechlorination of chlorocarbonates

0388291 - ÚOCHB 2013 DE eng A - Abstrakt
Marek, Aleš - Patil, Mahadeo Rajshekhar - Klepetářová, Blanka - Kohout, Ladislav - Elbert, Tomáš
A stereospecific pathway for the introduction of deuterium or tritium on the brassinosteroid skeleton by reductive dechlorination of chlorocarbonates.
11th International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds. Heidelberg: -, 2012. s. 55-55.
[International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds /11./. 09.09.2012-13.09.2012, Heidelberg]
Grant CEP: GA AV ČR IAA400550801
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: brassinosteroids * reductive dechlorination * tritium
Kód oboru RIV: CC - Organická chemie

A new and efficient procedure for the preparation of brassinosteroids labeled with hydrogen isotopes was developed. A four-step reaction sequence started with the selective oxidation of a 2,3-diol group to an alfa-hydroxy ketone, which was converted stereospecifically into a chlorocarbonate by reaction with triphosgene. A subsequent Pd-catalyzed reductive dechlorination with deuterium or tritium gas yielded labeled brassinosteroid 2,3-carbonates. The reaction sequence was completed by base-catalyzed hydrolysis of the cyclic carbonate.
Trvalý link: http://hdl.handle.net/11104/0217278